Sodium Hydroxide → Benzenepropanol, 2-(hydroxymethyl)- (9CI)

Participants

Reaction Steps

To a stirred solution of LAH (1.89 g, 49.77 mmol) in Et2O (40 mL) under N2 was cooled to 0° C. and was added AlCl3 (1.6 g, 11.8 mmol). The mixture was allowed to warm to room temperature and stirred for 30 minutes. A mixture of methyl 2-(3-methoxy-3-oxopropyl)benzoate (2 g, 9 mmol) in Et2O was added dropwise. The mixture was stirred overnight. Aqueous NaOH (1 N, 12 mL) was added at 0° C. The mixture was filtered and the cake was washed with EtOAc 3 times. The filtrate was dried and concentrated to give 3-(2-(hydroxymethyl)phenyl)propan-1-ol (1.46 g, 98%). 1H-NMR (CDCl3): 1.85 (m, 2H), 2.77 (m, 2H), 3.52 (m, 2H), 4.62 (s, 2H), 7.23 (m, 2H), 7.27 (m, 2H).

Provenance & Evidence